title: Bioactive and other sesquiterpenes from Chiloscyphus rivularis.
abstract: Bioassay-directed fractionation of the methyl ethyl ketone extract of Chiloscyphus rivularis yielded five new sesquiterpenes, 12-hydroxychiloscyphone (2), chiloscypha-2,7-dione (3), 12-hydroxychiloscypha-2,7-dione (4), chiloscypha-2,7,9-trione (5), and rivulalactone (6) in addition to the known sesquiterpenes, 4-hydroxyoppositan-7-one (7), chiloscyphone (1), and isointermedeol (8). The structure and stereochemistry of rivulalactone, a novel trinorsesquiterpene, was confirmed by its synthesis starting from 1. Compound 2 showed selective bioactivity in our yeast-based DNA-damaging assay and cytotoxicity to human lung carcinoma cells.
authors.affiliation: Department of Chemistry, Virginia Polytechnic Institute and State University, Blacksburg 24061, USA.
authors.forename: C
authors.initials: C
authors.lastname: Wu
authors.forename: A A
authors.initials: AA
authors.lastname: Gunatilaka
authors.forename: F L
authors.initials: FL
authors.lastname: McCabe
authors.forename: R K
authors.initials: RK
authors.lastname: Johnson
authors.forename: R W
authors.initials: RW
authors.lastname: Spjut
authors.forename: D G
authors.initials: DG
authors.lastname: Kingston
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology; D004249:DNA Damage; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010946:Plants, Medicinal / Q000737:chemistry*; D012717:Sesquiterpenes / Q000302:isolation & purification* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014407:Tumor Cells, Cultured
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D012717:Sesquiterpenes; C528862:isointermedeol